John Henry (10:18)
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This 1999 short was first released on video in 2002 as part of the "Disney's American Legends" anthology film. In 2015, it was released on Blu-ray/DVD as part of the "Walt Disney Animation Studios Short Films Collection," which is where I first saw it (in 2018).

Well, I've been at least vaguely aware of the legend of John Henry for pretty much as long as I can remember. Surely I've at least heard part of one of the many ballads that have been sung about him, and quite possibly some film adaptation of the legend prior to this, though I don't remember for certain. Nor did I ever remember any particular details of the story. (And of course, there are lots of different versions of the legend, which probably have somewhat different details.) It's also unclear whether or not the legends are based on a real person or not. But anyway, this version is narrated by John Henry's wife, Polly (voiced by Alfre Woodard, speaking, and Carrie Harrington, singing). She says that she and John were slaves, and after being freed by the Emancipation Proclamation, she forged the chains he had previously worn into a hammer. The two of them went looking for work and a place to settle. When they came upon a group of men who were building a railroad, having been given a contract to be paid for their work in land, John joins them. But then the owner of the railroad company shows up driving a steam-powered hammer (which in this version of the story is attached to a locomotive). He intends to finish the railroad himself, thereby negating the contract with the workers. The men want to riot, but John stops them, instead challenging the owner to a contest, to see whether he or the steam hammer could finish the job faster. I always thought it was just driving spikes into the rails, but in this version (and probably some of the original stories, which I was unaware of), they also both have to eventually pound their way through a mountain.

Well... you probably already know more or less how the story ends. But just in case, I won't spoil it. So, I'll just say it's a good story, with good animation, and good music.